(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester synthesis
- Product Name:(3E)-2,3-Dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylic acid methyl ester
- CAS Number:1168150-46-6
- Molecular formula:C18H15NO4
- Molecular Weight:309.32
1174335-83-1
1168150-46-6
1. Methyl (3E)-1-(2-chloroacetyl)-2,3-dihydro-3-(methoxyphenylmethylene)-2-oxo-1H-indole-6-carboxylate (390.0 g, 1.0109 mol) was suspended in methanol (1562 mL) and heated to reflux. 2. A solution of potassium hydroxide (23.35 g, 0.35 equiv) in methanol (196.8 mL) was added slowly and the reaction was stirred for 40 minutes at reflux. 3. After the reaction is complete, the reaction mixture is cooled to 5 °C and stirring is continued for 30 min to promote product precipitation. 4. The precipitated product was collected by filtration, washed with cold methanol and subsequently dried under vacuum to afford methyl (E)-3-(methoxy(phenyl)methylene)-2-oxo dihydroindole-6-carboxylate 292.2 g in 93.5% yield.
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Yield:1168150-46-6 93.5%
Reaction Conditions:
with methanol;potassium hydroxide for 0.666667 h;Reflux;
Steps:
8
l-(2-c oro-acetyl)-3-[l-methoxy-l-phenyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-lH- -6-carboxylic acid methyl ester (390.0 g / 1.0109 mol) was suspended in MeOH (1562 ml) and heated to reflux. A solution of KOH (23.35 g / 0.35 eq) in MeOH (196.8 ml) was added and the reaction was stirred for 40 minutes. After complete conversion the reaction was cooled down to 5°C and stirred for an additional 30 minutes. The precipitated product was filtered off, washed with cold MeOH and dried under vacuum to obtain 292.2 g (93.5 %) of 3 - [ 1 -methoxy- 1 -phenyl-meth-(E)-ylidene] -2-oxo-2,3 -dihydro- 1 H-indole-6-carboxylic acid methyl ester.
References:
WO2012/68441,2012,A2 Location in patent:Page/Page column 12; 13
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